


Until Tomorrow, Sweet Boy

by dudewhatswiththeshorts



Category: Supernatural
Genre: Anal Fingering, Bottom Dean, Bottom Dean Winchester, Dean is emotionally constipated, Dildos, Dirty Talk, Dom Castiel, Dom/sub, Fingerfucking, Humiliation, LITERALLY, M/M, Panty Kink, Sex Toys, Sub Dean, Sub Dean Winchester, Verbal Humiliation, almost four decades of repressed sexuality, has come to bite Dean in the ass, light panty kink
Language: English
Status: Completed
Published: 2016-08-21
Updated: 2016-08-21
Packaged: 2018-08-10 02:54:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,707
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7827604
Author URL: https://archiveofourown.org/users/dudewhatswiththeshorts/pseuds/dudewhatswiththeshorts
Summary: <blockquote class="userstuff">
              <p>Castiel knows that Dean has certain mental blocks that stop him from enjoying himself. He makes Dean overcome these blockages during play time after Dean came without permission.</p><p>Humiliation on Dean's part and dirty talk.</p>
            </blockquote>





	Until Tomorrow, Sweet Boy

**Author's Note:**

> I don't know what this is. It's not edited. I might add another chapter if y'all like it. Enjoy!!! :)

“Oh, Dean,” Cas clicks his tongue in disapproval, the sound causing shame and excitement to sizzle through Dean’s naked body. “You were being _such_ a good boy until now.”

Dean lets out a breath, trying to wrack his brain for a witty reply but coming up with nothing. He’s too focused on Cas. The angel is walking towards him and pushing him gently onto the bed behind him.

“What did you do wrong, lovely?” Cas asks, crawling on top of Dean. “Did you come without permission?”

Dean whines, cheeks coloring with shame. He nods tentatively, looking away from the angel.

Cas makes that disapproving noise again, that clicking sound with his tongue. “Use your words, Dean.” He takes Dean’s chin with two fingers and tilts it toward him. Dean keeps his eyes averted. “Look at me and use your words.”

Dean takes a shuddering breath, lets his green eyes travel up to Cas’ blue ones. “I…,” Dean trails off, swallowing before clearing his throat. “I came. Without permission. Sir.”

Cas’ stern face dissolves a little, his eyes smiling at Dean. “Good boy.”

The words cause Dean’s body to relax with shameful pleasure. Pleasing Cas makes him feel so… _right._ So special. Making Cas feel good by obeying him feels better than anything, even if it means screwing around with, well, a guy. You don’t just forget thirty-eight years of repressed bisexuality. Dean’s trying to come to terms with it, but it’s hard.

“Oh, sweetheart, this doesn’t mean you’re getting away from your punishment,” Cas says, breaking Dean out from his train of thought. “You’re being so good for me now, though, I don’t doubt you’ll get an award if you do what you’re told.”

Dean shudders, mutters a “thank you sir” and tries not to show how much his body is singing with excitement and anticipation.

Cas gets off of his sub. “Alright, Dean, up on your hands and knees,” he says.

At those words, Dean freezes. He averts his eyes again, knowing what that command is going to lead to.

“Dean?” Cas prompts.

The hunter closes his eyes. “No.”

Cas doesn’t say anything for a moment, waiting to see if Dean will safe word. When he’s sure that Dean isn’t going to, he speaks. “Resistance is only adding to your punishment, Dean.”

Finally, at that taunt, Dean gets up and kneels shakily, hanging his head in humiliation as Cas hums his approval. “You’re beautiful Dean. Hold yourself open so I can see you.”

Dean’s mouth runs dry and he digs his nails into his palms to ground himself before he carefully lays his face into his bed and takes two handfuls of asscheek, spreading himself so his hole is easily accessible. God, this was so wrong. Showing himself to another man so he could… _fuck him._ Like a girl. Like a slut. Dean feels a tear slip from his eye as Cas gently traces his fluttering hole.

“Mm, Dean, you say you don’t like this, but you do, don’t you?” Cas asks, knowing full well that Dean won’t answer. Dean wants to protest, but he can’t speak. His hole clenches involuntarily, seeking touch as Cas takes his finger off of him, which is enough of a response. The hunter hears lube being uncapped and applied to thick fingers. Soon, Cas’ finger has returned, rubbing and stroking and then finally _puuushing_ into Dean.

Dean makes a sound and Cas coos. “Oh, beauty, look at you,” he whispers. More pressure is consistent at Dean’s hole and another digit slips in. “Sucking me in. You beg for this more than you think, Dean Winchester. I can see your soul yearning for me. Yearning to be one with me.”

Dean shakes his head into the sheets, but then Cas is scissoring him and he’s pliant and loose against the sheets. He lets out a sob, clenches his hole, hating that he loves this. Loves Cas inside him and loves Cas whispering dirty, filthy things in his ear. “’m not. I-I don’t…,” Dean tries to stutter, but he doesn’t know what to say. Can’t string words together. Not while Cas is pressing a third finger in and is pressing against his walls and is getting him ready to stretch out on Cas’ cock or something bigger or maybe nothing at all because Cas likes to tease him like that. He likes to watch Dean cry and deny that the constant pressure inside him drives him crazy.

“Shh, sweetheart, I’m done. I’ll get something inside this needy hole of yours,” Cas soothes, and the words make Dean flush, his fingers slipping slightly from where they’re still holding him open, showing himself to Cas.

Cas leaves Dean alone on the bed, exposing himself to the room. Without Cas’ body heat, Dean feels vulnerable. More so than if Cas were there watching him. Because Cas is safe. Cas is home. Without him, Dean feels lost.

Dean isn’t left alone for long. Cas returns, letting Dean know he’s there with a firm hand on his lower back. “Alright, Dean,” the angle soothes, his hand gone as he slicks up whatever he has for Dean. “This is staying in until tomorrow morning, understand?”

Dean nods, afraid to speak because he knows if he talks he’ll beg for Cas’ cock and he shouldn’t want to, shouldn’t want that. His cock is hard and curving toward his stomach and Cas has ignored it. And honestly, so has Dean. He’s been too caught up with Cas’ fingers in his ass to notice how fucking hard he was. Jesus Christ, he’s gonna come from his as alone if Cas doesn’t finish things up. He’s gonna come with something inside of him, like a woman would. Dean would be lying if that thought didn’t make him whimper, didn’t force another wave of wrongness to travel up from his toes.

Suddenly there’s something pressing at his hole, thicker than Cas’ fingers. The stretch makes Dean flinch, makes him cry out and Cas chuckles. “Look at you,” the angle murmurs, “Eating it up. You’re so greedy. How is this punishment when you love every second?”

The dildo pushes into Dean’s hole slowly, never ending, filling him up completely, pushing against his walls and then–

“ _Oh! Cas, ohhhhh,”_ he moans.

Cas smiles. “Baby, did I find your good spot?”

Dean nods frantically into the bedsheets moaning as Cas twists and jabs at his prostate, unable to keep his noises in.

“I love hearing you sing, Dean,” Cas says.

Dean shakes, on the edge of blowing his load of coming all over his stomach and bed and shaking thighs.

Cas pulls back after one harsh thrust, pushing in until the dildo is completely inside Dean’s hole. “There we go.”

Cas moves away from his sub, taps his arms to let him know he can let them down. Dean does, flops his hands to his sides, but he keeps his face buried in the bed, his ass in the air, shaking and needy and humiliated beyond belief. There was a giant rubber dick stuffed in his ass and his dick was leaking beyond belief and he was about to just _burst_ , come all over everything.

Just by being filled. By being stuffed full by his dom, by _Cas_.

Yes. That was it. It was all about pleasing Cas, about making him feel good. He felt good if Cas felt good. But Cas wasn’t the ones with fingers up his ass. Hell, Cas wasn’t fucking him with his own cock. Cas was simply pleasing Dean and the hunter was still all over it.

“Dean?” Cas asks tenderly, coming up behind him. “Is it too much?”

Dean shakes his head.

“I need you to use your words, please.” There’s a firm hand against him.

“I’m green.”

A breath of relief.

“Come on, lay down on your stomach. Your ass is sore from the rough treatment.”

Dean shakes his head, inhales sharply at Cas’ words.

“Dean. Lay down. Relax.”

“No.”

“This is an order, Dean. You need to lay down.” Cas uses a voice of authority, one that causes Dean to gasp and shiver from his place with his ass still in the air.

“ _I can’t_ ,” Dean rasps, too embarrassed to tell Cas his real problem, but instead of ignoring what Dean’s saying, Cas presses on.

“Are you injured? I need you to be serious about this. If you’re hurt, you need to safe word–”

“ _No, Cas,_ ” Dean hisses, lifting his head up and making eye contact with the angel, “If my dick touches this bed– if it fucking touches anything –I’m going to _come_ , _okay_?”

The silence in the room is tangible, Dean’s face red and his cheeks stained with tears from the shame of it all.

Cas watches Dean, smiles a bit, lays a hand down and rests it on Dean’s cheek. “Can’t come yet, Dean.” The hunter swallows, shakes as Castiel smiles, small and sneaky. “Let’s get you on your back, shall we?”

Dean allows Cas to turn him slowly onto his back, jolting when the dildo shifts and brushes up against his prostate. It’s nothing like Cas’ fingers. Instead of it moving in and out, thick and warm and shamefully perfect, it’s solid and long and plastic.

“Do you need the cock ring?” Castiel asks.

Oh God, the cock ring was worse than the dildo because it proved that Dean needed restraint. That he couldn’t be a good sub by himself. That he needed to hold himself back from coming because of his hole full of fake cock.

“No, sir.”

Cas purrs happily. “Good boy.”

Minutes pass, but they feel like hours. Cas is in bed with Dean, not touching him, but giving Dean a solid presence while he calms down from his Dom’s touch. When Dean’s finally under control he lets Cas help him up and into his panties– little cotton things that Cas insisted he indulge in –and then into his jeans. He makes a pained noise when he stuffs his half-hard dick into the confinement of the pants, and Cas makes a soft, comforting noise in response. 

“Until tomorrow morning, sweet boy,” Cas reminds him. 

Dean takes another shaking breath, nods. He can make it until tomorrow.

He’d do anything for Castiel.

**Author's Note:**

> Check out my tumblr: dudewhatswiththeshorts.tumblr.com


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